Trifluoroacetic acid → HCID 66691911, compound

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-(2-Methoxyphenyl)-5-methyl-1,2-oxazole-4-carboxylic acid	HCID 6484100	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	HCID 66692536	HCID 66692536	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 66691911	HCID 66691911	—

Reaction Steps

To a solution of 5-chloro-3-nitro-6-(piperazin-1-yl)pyridin-2-amine, TFA (0.192 mmol) in DMF (2 ml) was added DIEA (0.134 ml, 0.768 mmol), 3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxylic acid (44.8 mg, 0.192 mmol) and HATU (73.0 mg, 0.192 mmol). The reaction was stirred at room temperature for 1 h. The reaction mixture was purified by preparative HPLC to afford 69 mg (73.7% for 3 steps) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 8.25 (1H, s), 7.58 (1H, dd, J=7.5, 1.7 Hz), 7.52-7.39 (1H, m), 7.08-7.06 (1H, m), 6.97 (1H, d, J=7.9 Hz), 3.79 (3 H, s), 3.72 (2H, br. s.), 3.55 (2H, br. s.), 3.16 (2H, br. s.), 2.98 (2H, br. s.), 2.55 (3H, s).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08362004B2
Source dataset	uspto-grants-2013_01
ORD ID	ord-598cc207b5e340e4988a9e1bf098100c
Source note	uspto-grants-2013_01